Synthesis of phthalocyanines crosswise-substituted with two alkylsulfanyl and two amino groups

Crosswise-substituted phthalocyanines (4, 4a-c) with two nitro and two dodecylsulfanyl groups are synthesized by a 2:2 condensation of 1,3-dihydro-1,3-diimino-6-(n-dodecylsulfanyl)isoiminoindolenine (2) with 6-nitro-1,3,3-trichloroisoindolenine (3) in the presence of sodium methoxide, hydroquinone and triethylamine. Nitro substituents are reduced to amines by sodium sulfide and condensation of the amine groups with ferrocenylaldehyde results in a new pc with two ferrocenylimino substituents, The novel compounds are characterized by UV/vis, mass and H-1-NMR spectroscopy.